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aReagents and conditions: (i) ClCH2CN/HCl (conc), 90 °C, 24 h; (ii) TsCl, DMAP, Et3N, rt, 3 h; (iii) i-PrOH, 45 °C, 6 h; (iv) KOAc, 55 °C, 6 h; (v) Pd/C, H2, rt, 2 h; (vi) ClCH2COCl/K2CO3, acetone, 0 °C, 1 h; (vii) K2CO3/DMF, 100 °C, 1 h; (viii) NaOH (10%), rt, 1 h; (ix) Br(CH2)3COOEt/Cs2CO3, 90 °C, 4 h; (x) NH2OH·HCl, 0 °C, 4 h.
